4-(Trifluoromethyl)phenyl isocyanate → HCID 71227246, compound

HRID 2370023Notes

Reaction equation

HRID 2370023 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:23](=[O:35])CC3C4C(=CC=CC=4)N(C)C=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[N:36]([C:39]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=1)=C=O>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:23]([NH:36][C:39]3[CH:44]=[CH:43][C:42]([C:45]([F:46])([F:47])[F:48])=[CH:41][CH:40]=3)=[O:35])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 71226691HCID 71226691, compound2×

Product 1

HCID 71227246HCID 71227246, compound

Procedure

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethyl)phenyl)urea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (50 mg, 0.17 mmol) and 1-isocyanato-4-(trifluoromethyl)benzene (31.3 mg, 0.17 mmol) according to General Procedure G to give 18 mg (22.1%) of white solid. Anal. Calcd. for C26H30F3N5O m/z 458.2, found: 486.3 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.53 (d, J=8.8 Hz, 2H), 7.45 (d, J=8.6 Hz, 2H), 7.25 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 3.64 (m, 1H), 3.51 (m, 2H), 3.05 (m, 1H), 2.70 (m, 1H), 2.12 (m, 1H), 1.99 (m, 3H), 1.83 (m, 3H), 1.67 (m, 3H), 1.39 (m, 6H).

Sources & evidence

ORD record
ord-74cb03490c044cee929332425ecb2c0c
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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